The privileged lives of the real 'Rich Kids of Instagram' — including Tiffany Trump

Aspiring designer Andrew
Warren and his curated crew of privileged friends — a Trump, a
Kennedy and a Matisse among them — are serious about leveraging
social media to find their purpose, but often, they just feel
seriously misunderstood.Alex John
Beck

Down a private drive in the Hamptons, past a sign that reads
“Warren on the Cobb,” sits a sprawling clapboard house, complete
with a sparkling baby-blue pool, monogrammed deck furniture and
the pièce de résistance floating expectantly in the
center of the pool: a giant inflatable swan.

It’s raining today, the second weekend of the summer, and the
house is full.

The Ringleader: Andrew Warren

A Japanese camera crew has flown in to interview Andrew Warren,
the 22-year-old grandson of fashion mogul David Warren.

The elder Warren made his name in the ’70s with the sort of prim
and polished “social occasion” dresses that women bought at
Bloomingdale’s and Saks.

The younger Warren is a budding fashion mogul himself, with a
collection of edgy ready-to-wear pieces he launched in 2013
called Just Drew.

Though the reporter, whom Warren calls “like the Katie Couric of
Japan,” is ostensibly here to talk about the line, her questions
inevitably return to the topic of Warren’s friends, a young,
beautiful, pedigreed group that appears throughout Warren’s
widely followed Instagram account.

Warren is at once slighted and nonplussed. He knows his friends
are interesting to strangers. He’s helped make them that way,
casting them in his lookbooks and leveraging their equally famous
names to a collective advantage with the help of social media.

Warren handpicks his crew — which at the moment includes
Gaia Matisse, Kyra Kennedy, Reya Benitez and Tiffany Trump — as
if putting together a jigsaw puzzle, “weeding out,” as he says,
the ones who don’t fit in.

The photos they share on social media tell the story of an
enviable set of lives intertwined, sipping rosé in infinity pools
by day, sipping rosé on balconies overlooking the Marais by night
— a picture-perfect posse of wealthy progeny.

And yet, Warren insists, they’re not all about popping bottles
and digging into their trust funds. They have professional
ambitions, too. In fact, it’s that shared desire to pave their
own way and prove they’re not just spoiled brats with Birkins
that connects this fivesome the most.

They can’t help it if, as Matisse says, they also happen to “look
good on a swan.”

The Aspiring Actress: Gaia Matisse

Matisse, who met Warren in middle school, is
the great-great-granddaughter of French artist Henri Matisse.

She sees broadcasting her daily escapades on social media as a
strategy, rather than a brazen ego-feed. She’s an aspiring
actress and model, and who knows? Perhaps the scantily clad
selfies she shares with her 13,000 Instagram followers will
upthrust her profile; score her the right agent; land her
future movie roles.

Despite her pedigree — her father, Alain Jacquet, who died in
2008, was also an artist — Matisse says a career as a
painter was never in the cards for her. “Acting is my art form,”
she professes, batting her blue-mascara-coated lashes.

She’s been working with “Bradley Cooper’s acting coach,” she
points out, since she was 16. “I met her randomly when I was
having dinner with Mickey Rourke,” she says. “I just need to get
an agent now.”

Matisse insists that she didn’t grow up overindulged.

She went to public school in New York City and
recounts stories of shopping with her mother for $15
sweatpants. “ ‘Matisse’ was never a thing,” she says, though
she’s opted to go by her mother’s more famous last name.
“Money was never talked about.”

The Cool Girl: Reya Benitez

Reya Benitez, the 23-year-old daughter of John “Jellybean”
Benitez and a friend of Warren’s since high school, tells a
similar story.

Her father was the resident DJ for Studio 54 and has
produced tracks for Madonna and Whitney Houston. Benitez
points out that she started hostessing at her mother’s
restaurant, The Coffee Shop, when she was 13. These days, she
works at a concierge management company but is toying with the
idea of following in her father’s footsteps as a DJ.

She’s eagerly working to grow her social media handle, @ReyaBenitez, which currently has some 2,200
followers. “Social media lets [people] see who we are through
what we do,” she says. “Everyone always says [my DJ name] should
be Little Bean, but I want to create my own name without any help
from my father. I don’t want to be overshadowed by him.”

Social media is, of course, what makes this generation of famous
progeny different from its predecessors, both offering them
opportunity and presenting a challenge. While it’s hard to
imagine, say, Sofia Coppola posting figure-flaunting photos of
herself to collect followers, maybe she would have, given the
option.

For Warren and his crew, it’s hard not to harness the power
of social media, now that it exists — especially when every
day is as Instagram-worthy as it is for them. That said,
there are plenty of people who accuse the group of
flashing the wealth they did nothing to earn, and many
have tried to turn their lives into something of a punch
line.

Warren’s feed is routinely pilfered for images that end up
on @RichKidsofInstagram, an anonymous
account that highlights the most obnoxious and
rubbernecking-worthy posts from wealthy children on the
Web.

While this annoys Warren — it’s not about being showy; it’s just
how life is and besides, he says, “I just really like taking
photos”— he acknowledges that the attention is free, and not
unwanted, promotion for his brand.

He has vast, lofty goals for Just Drew (“I could see it
becoming something like a Givenchy,” he says) that he thinks
social media will help him achieve. And it very well might: Many
of his regrammed photos feature the girls in Just Drew, posed
alongside the designer. Over the last year, Warren’s line
has expanded into two boutiques. He’s currently in talks with
international distributors, an accomplishment he chalks up to
relationships he’s cultivated. “Everyone knows Andrew. All his
friends come in and buy,” says Jeff Goldstein, the owner of
Blue & Cream, the first boutique to carry his line.

The Party Girl: Kyra Kennedy

Kyra Kennedy, the 19-year-old daughter of Robert F. Kennedy Jr.
and the late Mary Kathleen Richardson, was scooped up by Warren
in Aspen last December and quickly became a fixture of Warren’s
feed, appearing in photos at nightclubs and in hotel suites.

Kennedy experienced her first bout of infamy earlier this year
after a newspaper article claimed she attempted to use her older
half-sister’s passport to get into a nightclub.

When she was denied, she allegedly responded, “I’m a
Kennedy. Google me.” (The drama “was basically fabricated,”
she says.) Still, the embarrassment kept her from attending an
internship for two weeks. “I couldn’t bear to see anyone,”
she says. “My dad said, ‘I’m sorry, but hiding is not the right
thing to do. You just have to face the truth and be like, this is
not me. This is not true.’ ”

You could say she’s stopped hiding. Kennedy’s Instagram profile states, “I’m
a mess but I make it look so good,” and indeed, in it, life
looks pretty good.

There she is wearing Marni in Montauk, or cozying up to actress
Bella Thorne at the Chateau Marmont. Her dad has called and
requested that she “clean up her Instagram,” but as far as
Kennedy, a freshman at FIT, is concerned, she’s just having a
good time. And Warren would have to agree. “We have fun with it,”
he says. “If people have something negative to say, we’re not
asking them to follow in the first place.

Still, she’s doing something right — or at least crowd-pleasing.
She’s got 30,000 followers, even if her dad is not among them. “I
don’t know what it’s like to have a typical father figure,” says
Trump. “He’s not the dad who’s going to take me to the beach and
go swimming, but he’s such a motivational person.” She’s debating
whether to go to business school or law school after college.

It’s Saturday night in Southampton — the perfect
excuse for a dinner party. Warren has invited 25 friends to
a buzzy East End restaurant in celebration of his successful Just
Drew trunk show, which took place earlier today at a local
boutique.

A society photographer is snapping away as bottles of rosé float
across the table. “Wait!” Matisse yells to the lensman. She grabs
the hand of Peter Brant Jr., son of billionaire businessman Peter
M. Brant, and points to a decorative hedge. “This is a great
picture. Take this!” She dips her head back and falls,
dramatically, into a bush.

While there may be no such thing as bad press, fast fame isn’t
necessarily on the agenda. Warren and the girls have been
approached by producers interested in building a reality show
around them, but they’ve turned up their collective noses at the
idea. “I think that it’s just selling yourself, and it’s not an
attractive look. I don’t believe in it,” Kennedy sniffs. Adds
Trump, “You have to think long term. It’s easy money, but
…”

“But,” interjects Matisse, “it conflicts so much with all of
our different personal goals. Besides, it’s not about money or
fame, it’s about our friendships. It’s about us being
amazing people and loving each other. That’s what it’s
about.”